In the 1990's, Mike Diana published the comic zine Boiled Angel from his home state of Florida. In 1995, Diana was arrested and the zine became the subject of an obscenity trial. Diana was judged gulty. Aside from being fined $3,000.00, and being required to perform 1,280 hours of community service, remain employed, and see a pyschiatrist at his own expense, the state forbid him to draw for his own personal use. Diana left Florida before his probation period was finished and moved to New York City.

Mike Diana has been profiled in many zines, including Ben Is Dead, and his work has appeared in zines such as WoRMfEA$t!. He has also had his comics published in several anthologies including Spice Capades, published by Fantagraphics and edited by Queen Itchie, and Zero Zero.

In Florida, Mike Diana had made several films on video tape which he sold through mail order. Upon moving to New York Mike Diana began appearing in films by underground filmmakers. In 1996, Peter Cramer and Jack Waters made the experimental documentary Introducing Mr. Diana. He has also appeared in two Nick Zedd films, Why Do You Exist? (1998) and Ecstasy In Entropy (1999). In 2007 the film Kill The Artist by Andreas Troeger was released, an experimental documentary dealing with censorship and the arts featuring Mike Diana, among other artists whose works have been banned, resulted in censorship, or seized at the border.